6-De-oxy-α-l-talopyran-ose.

X-ray crystallography showed that the title compound, C(6)H(12)O(5), crystallizes in the α-pyran-ose form with the six-membered ring in a chair conformation. The crystal structure exists as a three-dimensional hydrogen-bonded network of mol-ecules with each mol-ecule acting as a donor and aceptor for four hydrogen bonds. The absolute configuration was determined by the use of l-fucose as starting material.

Related literature

For related literature, see: Beadle et al. (1992 ▶); Izumori (2002 ▶, 2006 ▶); Granstrom et al. (2004 ▶); Yoshihara et al. (2008 ▶).

Experimental

Crystal data

C6H12O5

M = 164.16

Orthorhombic,

a = 6.4939 (3) Å

b = 7.4874 (4) Å

c = 14.8382 (8) Å

V = 721.47 (6) Å3

Z = 4

Mo Kα radiation

μ = 0.13 mm−1

T = 150 K

0.25 × 0.25 × 0.02 mm

Data collection

Nonius KappaCCD diffractometer

Absorption correction: multi-scan DENZO/SCALEPACK (Otwinowski & Minor, 1997 ▶) T min = 0.97, T max = 1.00 (expected range = 0.967–0.997)

4390 measured reflections

968 independent reflections

863 reflections with I > 2.0σ(I)

R int = 0.037

Refinement

R[F 2 > 2σ(F 2)] = 0.029

wR(F 2) = 0.072

S = 1.03

968 reflections

100 parameters

H-atom parameters constrained

Δρmax = 0.24 e Å−3

Δρmin = −0.21 e Å−3

Data collection: COLLECT (Nonius, 1997–2001 ▶).; cell refinement: DENZO/SCALEPACK (Otwinowski & Minor, 1997 ▶); data reduction: DENZO/SCALEPACK; program(s) used to solve structure: SIR92 (Altomare et al., 1994 ▶); program(s) used to refine structure: CRYSTALS (Betteridge et al., 2003 ▶); molecular graphics: CAMERON (Watkin et al., 1996 ▶); software used to prepare material for publication: CRYSTALS.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808019582/lh2652sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808019582/lh2652Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C6H12O5	F000 = 352
Mr = 164.16	Dx = 1.511 Mg m−3
Orthorhombic, P212121	Mo Kα radiation λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 890 reflections
a = 6.4939 (3) Å	θ = 5–27º
b = 7.4874 (4) Å	µ = 0.13 mm−1
c = 14.8382 (8) Å	T = 150 K
V = 721.47 (6) Å3	Plate, colourless
Z = 4	0.25 × 0.25 × 0.02 mm

Nonius KappaCCD diffractometer	863 reflections with I > 2.0σ(I)
Monochromator: graphite	Rint = 0.037
T = 150 K	θmax = 27.5º
ω scans	θmin = 5.2º
Absorption correction: multi-scanDENZO/SCALEPACK (Otwinowski & Minor, 1997)	h = −8→8
Tmin = 0.97, Tmax = 1.00	k = −9→9
4390 measured reflections	l = −19→19
968 independent reflections

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.029	Method = Modified Sheldrick w = 1/[σ2(F2) + ( 0.04P)2 + 0.04P] ,where P = (max(Fo2,0) + 2Fc2)/3
wR(F2) = 0.072	(Δ/σ)max = 0.0002
S = 1.03	Δρmax = 0.24 e Å−3
968 reflections	Δρmin = −0.21 e Å−3
100 parameters	Extinction correction: None
Primary atom site location: structure-invariant direct methods

	x	y	z	Uiso*/Ueq
O1	0.95002 (16)	0.08900 (18)	0.35376 (7)	0.0210
C2	0.7416 (2)	0.1250 (2)	0.32982 (10)	0.0175
C3	0.6113 (3)	0.1509 (3)	0.41551 (10)	0.0188
O4	0.65011 (17)	0.31964 (16)	0.45740 (7)	0.0183
C5	0.6150 (2)	0.4717 (2)	0.39897 (10)	0.0194
C6	0.6412 (3)	0.6382 (3)	0.45454 (12)	0.0271
C7	0.7657 (2)	0.4593 (2)	0.32003 (10)	0.0187
C8	0.7208 (2)	0.2889 (3)	0.26846 (10)	0.0186
O9	0.85143 (18)	0.26675 (18)	0.19178 (7)	0.0243
O10	0.97297 (17)	0.45445 (18)	0.35319 (8)	0.0232
O11	0.40458 (18)	0.1333 (2)	0.39115 (8)	0.0254
H21	0.6937	0.0193	0.2985	0.0197*
H31	0.6474	0.0567	0.4621	0.0197*
H51	0.4756	0.4675	0.3773	0.0236*
H61	0.6179	0.7441	0.4188	0.0406*
H62	0.5480	0.6346	0.5057	0.0398*
H63	0.7791	0.6452	0.4743	0.0401*
H71	0.7508	0.5628	0.2786	0.0214*
H81	0.5761	0.2938	0.2475	0.0221*
H7	0.8826	0.3664	0.1753	0.0374*
H8	0.9866	0.1914	0.3632	0.0333*
H10	1.0243	0.5538	0.3399	0.0350*
H1	0.3258	0.1436	0.4383	0.0408*

	U11	U22	U33	U12	U13	U23
O1	0.0198 (5)	0.0204 (7)	0.0229 (6)	0.0030 (5)	−0.0010 (5)	−0.0005 (5)
C2	0.0184 (7)	0.0188 (9)	0.0153 (7)	−0.0001 (8)	−0.0013 (6)	−0.0015 (6)
C3	0.0209 (8)	0.0186 (9)	0.0169 (7)	−0.0037 (7)	0.0005 (6)	−0.0021 (7)
O4	0.0223 (5)	0.0178 (7)	0.0150 (5)	−0.0008 (5)	−0.0006 (5)	0.0007 (5)
C5	0.0220 (8)	0.0184 (9)	0.0179 (7)	0.0019 (8)	−0.0015 (7)	0.0002 (7)
C6	0.0378 (10)	0.0202 (10)	0.0232 (8)	0.0022 (9)	0.0025 (9)	−0.0040 (7)
C7	0.0183 (7)	0.0202 (9)	0.0176 (7)	0.0031 (7)	0.0006 (7)	0.0029 (7)
C8	0.0197 (7)	0.0212 (10)	0.0149 (7)	0.0011 (7)	0.0013 (6)	−0.0005 (7)
O9	0.0335 (6)	0.0213 (7)	0.0180 (5)	0.0043 (6)	0.0087 (5)	0.0025 (5)
O10	0.0195 (5)	0.0195 (7)	0.0306 (6)	−0.0026 (5)	−0.0015 (5)	0.0023 (6)
O11	0.0199 (5)	0.0331 (8)	0.0233 (5)	−0.0074 (6)	0.0028 (5)	−0.0047 (6)

O1—C2	1.4250 (19)	C6—H61	0.966
O1—H8	0.815	C6—H62	0.971
C2—C3	1.540 (2)	C6—H63	0.944
C2—C8	1.534 (2)	C7—C8	1.516 (2)
C2—H21	0.969	C7—O10	1.4334 (19)
C3—O4	1.430 (2)	C7—H71	0.994
C3—O11	1.3965 (19)	C8—O9	1.4288 (18)
C3—H31	1.015	C8—H81	0.990
O4—C5	1.449 (2)	O9—H7	0.811
C5—C6	1.504 (2)	O10—H10	0.839
C5—C7	1.529 (2)	O11—H1	0.870
C5—H51	0.962
C2—O1—H8	98.1	C5—C6—H62	109.6
O1—C2—C3	109.88 (12)	H61—C6—H62	110.8
O1—C2—C8	112.50 (13)	C5—C6—H63	108.9
C3—C2—C8	109.93 (14)	H61—C6—H63	105.9
O1—C2—H21	105.7	H62—C6—H63	110.5
C3—C2—H21	108.8	C5—C7—C8	108.34 (14)
C8—C2—H21	109.9	C5—C7—O10	109.84 (12)
C2—C3—O4	111.93 (14)	C8—C7—O10	109.43 (14)
C2—C3—O11	107.62 (12)	C5—C7—H71	111.3
O4—C3—O11	111.43 (15)	C8—C7—H71	109.0
C2—C3—H31	110.4	O10—C7—H71	108.9
O4—C3—H31	106.1	C2—C8—C7	110.89 (12)
O11—C3—H31	109.4	C2—C8—O9	109.12 (13)
C3—O4—C5	113.97 (11)	C7—C8—O9	112.67 (13)
O4—C5—C6	107.79 (12)	C2—C8—H81	107.4
O4—C5—C7	108.05 (13)	C7—C8—H81	108.0
C6—C5—C7	113.45 (14)	O9—C8—H81	108.5
O4—C5—H51	108.8	C8—O9—H7	106.4
C6—C5—H51	108.5	C7—O10—H10	105.7
C7—C5—H51	110.1	C3—O11—H1	110.4
C5—C6—H61	111.2

D—H···A	D—H	H···A	D···A	D—H···A
O9—H7···O1i	0.81	2.04	2.818 (2)	162
O1—H8···C7	0.82	2.55	3.061 (2)	122
O1—H8···O10	0.82	1.98	2.740 (2)	156
O10—H10···O9i	0.84	1.85	2.686 (2)	177
O11—H1···O4ii	0.87	1.94	2.812 (2)	177

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O9—H7⋯O1i	0.81	2.04	2.818 (2)	162
O1—H8⋯O10	0.82	1.98	2.740 (2)	156
O10—H10⋯O9i	0.84	1.85	2.686 (2)	177
O11—H1⋯O4ii	0.87	1.94	2.812 (2)	177

Symmetry codes: (i) ; (ii) .